Dimethylformamide → HCID 178437537, compound

HRID 412708Notes

Reaction equation

HRID 412708 reaction equation
C(O[C:4]([CH2:6][C:7]1[NH:8][C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][C:10]=2[N:25]=1)=O)C.Cl.[NH2:27][C:28]1[CH:29]=[C:30]([NH:35][C:36]([NH2:38])=[NH:37])[CH:31]=[CH:32][C:33]=1[NH2:34].[CH3:39]N(C)C=O>C(#N)C>[NH:35]([C:30]1[CH:31]=[CH:32][C:33]2[NH:34][C:39]([CH:6]([C:7]3[NH:8][C:9]4[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=5)=[O:16])[CH2:11][C:10]=4[N:25]=3)[CH3:4])=[N:27][C:28]=2[CH:29]=1)[C:36]([NH2:38])=[NH:37]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 178470779HCID 178470779, compoundHCID 178479388HCID 178479388, compound

Product 1

HCID 178437537HCID 178437537, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture comprising benzyl 2-ethoxycarbonylmethyl-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate (1.7 g, 4.8 mmol), N-(3,4-diaminophenyl)guanidine hydrochloride (0.8 g, 4.0 mmol) and dimethylformamide (2 mL) heated in an oil bath at 185° C. and stirred under a nitrogen atmosphere for 2.5 hours. The mixture was cooled to room temperature and poured into stirring acetonitrile ( 150 mL) to give a precipitate. The precipitate was washed with additional acetonitrile and diethyl ether (150 mL), collected by filtration and dried in vacuo to give an off white solid. The solid was purified by preparative reverse phase HPLC to provide benzyl 2-[1-(5-guanidino-1H-benzoimidazol-2-yl)ethyl]-1,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carboxylate as a white solid (1.0 g, 55% yield); LRMS(ESI): Calculated for C24H26N8O2: 458.5; Found (MH+): 459.2.

Workup

  1. additionpoured
  2. customto give a precipitate
  3. washThe precipitate was washed with additional acetonitrile and diethyl ether (150 mL)
  4. filtrationcollected by filtration
  5. customdried in vacuo
  6. customto give an off white solid
  7. customThe solid was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-433c98f0742b4d9eb6400c26a76df11f
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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